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Vacation Rentals in Kailua, HI

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
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Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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51 Trusted Kailua Rentals
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5 Bedrooms, 6 Bathrooms, Sleeps 14
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You added Place in Paradise - Large 5 Bedroom Beach Front on Kailua Bay to your Saves list
from
$1,500
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
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You added Exec Eco Friendly Beachside Home w/ Swimming Pool to your Saves list
from
$695
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 9
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You added Luxurious Lanikai beachside home with pool to your Saves list
from
$750
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
from
$2,500
Per Night
10 Bedrooms, 11 Bathrooms, Sleeps 18
Free gift worth $249
from
$5,200
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
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You added Kailua Beach Front Home BEST VIEWS & BEST BEACH to your Saves list
from
$1,200
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 14
from
$600
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
from
$329
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 16
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You added Kailua Estate-Gated & Gorgeous! 4000 sq ft w/pool to your Saves list
from
$900
Per Night
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3 Bedrooms, 3 Bathrooms, Sleeps 7
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You added Beautiful Beach Villa w/ Swimming Pool & Jacuzzi to your Saves list
from
$395
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
from
$255
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
from
$185
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
from
$90
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
from
$125
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 22
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You added 5 minutes from America's Best Beach - (Kailua) to your Saves list
from
$75
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
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You added Kailua-Absolutely Oceanfront-Watrfall Pool-$199 to your Saves list
from
$199
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
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You added Ocean Air ,Largest Swimming Pool in the world to your Saves list
from
$160
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
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You added Charming 2 Bdrm Beachside Villa with Swimming Pool to your Saves list
from
$265
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
from
$85
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
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You added Kailua Beach House 6+BR, Beachfront, Pool to your Saves list
from
$1,575
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
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You added Peaceful property in lush tropical setting to your Saves list
from
$175
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Tropical Luxury 2Bed/2Bath Steps to Kailua Beach to your Saves list
from
$275
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
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You added 5 minutes walk to Kailua Beach -Kailua Hale Ohana to your Saves list
from
$108
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
from
$165
Per Night
Studio, 1 Bathroom, Sleeps 2
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You added Large studio in beautiful Lanikai; steps to beach to your Saves list
from
$139
Per Night
Studio, 1 Bathroom, Sleeps 4
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You added The Suite Spot - Kailua Bay & Mountain Views, Oahu to your Saves list
from
$175
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
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You added Ehu Kai - Luxurious Cottage Kailua Beachfront to your Saves list
from
$425
Per Night
7 Bedrooms, 9 Bathrooms, Sleeps 14
Free gift worth $249
from
$6,500
Per Night
5 Bedrooms, 7 Bathrooms, Sleeps 10
from
$3,500
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 14
from
$815
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
from
$135
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 8
from
$1,080
Per Night
8 Bedrooms, 10 Bathrooms, Sleeps 16
from
$9,000
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
1 night free with a 6 day stay
from
$900
Per Night
6 Bedrooms, 6 Bathrooms, Sleeps 16
from
$2,500
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
from
$906
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
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You added Hale Kahakai - Long Term Rental Only - Hawaiian Charmer on Kailua Beachfront to your Saves list
from
$332
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
from
$860
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
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You added Sea Grape Hale - Delightful Kama`aina Home Beachside in Kailua to your Saves list
from
$495
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
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You added Kaha Cottage - Serenity, Comfort and Style to your Saves list
from
$249
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
from
$900
Per Night
8 Bedrooms, 10 Bathrooms, Sleeps 16
from
$8,000
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Save
You added Serenity Cottage - Cozy Cottage Kailua Beachfront to your Saves list
from
$395
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
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You added Blissful Kailua - Oceanfront Beauty with a Pool to your Saves list
from
$1,600
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 8
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You added Ho 'onanea - Exquisite Balinese Beachside with Pool to your Saves list
from
$2,500
Per Night
1 Bedroom, 3 Bathrooms, Sleeps 4
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You added Bali Hawaii, 2,000 sq ft, private pool, by beach to your Saves list
from
$300
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
from
$775
Per Night
6 Bedrooms, 1 Bathroom, Sleeps 11
from
$700
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Save
You added Kailua Hale Nalu Palekaiko, Best Beaches, Pool to your Saves list
from
$425
Per Night
Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.

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